Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes

Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes—a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama–Denmark coupling to give (Z)-alkenyl polyene motifs found in bioactive natural products. T...

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Detalles Bibliográficos
Autores principales: Elbert, Bryony L, Lim, Diane S W, Gudmundsson, Haraldur G, O'Hanlon, Jack A, Anderson, Edward A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2014
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4531823/
https://www.ncbi.nlm.nih.gov/pubmed/24899240
http://dx.doi.org/10.1002/chem.201403255
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author Elbert, Bryony L
Lim, Diane S W
Gudmundsson, Haraldur G
O'Hanlon, Jack A
Anderson, Edward A
author_facet Elbert, Bryony L
Lim, Diane S W
Gudmundsson, Haraldur G
O'Hanlon, Jack A
Anderson, Edward A
author_sort Elbert, Bryony L
collection PubMed
description Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes—a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama–Denmark coupling to give (Z)-alkenyl polyene motifs found in bioactive natural products. The ring size of the silane is crucial: five-membered cyclic siloxanes also couple under fluoride-free conditions, whilst their six-membered homologues do not, enabling orthogonality within this structural motif.
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spelling pubmed-45318232015-08-15 Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes Elbert, Bryony L Lim, Diane S W Gudmundsson, Haraldur G O'Hanlon, Jack A Anderson, Edward A Chemistry Communications Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes—a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama–Denmark coupling to give (Z)-alkenyl polyene motifs found in bioactive natural products. The ring size of the silane is crucial: five-membered cyclic siloxanes also couple under fluoride-free conditions, whilst their six-membered homologues do not, enabling orthogonality within this structural motif. WILEY-VCH Verlag 2014-07-07 2014-06-04 /pmc/articles/PMC4531823/ /pubmed/24899240 http://dx.doi.org/10.1002/chem.201403255 Text en © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. https://creativecommons.org/licenses/by/4.0/ © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Elbert, Bryony L
Lim, Diane S W
Gudmundsson, Haraldur G
O'Hanlon, Jack A
Anderson, Edward A
Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes
title Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes
title_full Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes
title_fullStr Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes
title_full_unstemmed Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes
title_short Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes
title_sort synthesis of cyclic alkenylsiloxanes by semihydrogenation: a stereospecific route to (z)-alkenyl polyenes
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4531823/
https://www.ncbi.nlm.nih.gov/pubmed/24899240
http://dx.doi.org/10.1002/chem.201403255
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